This invention relates to a novel method of fixing acetaldehyde in grape flavors and producing novel grape flavored consumable materials by means of the formation of 1-n-butoxy-1-ethanol acetate which acts as a generator responding to conditions of use in grape flavored food products to yield acetaldehyde, in conjunction with 2-phenyl-3-carboethoxyfuran and/or bis(cyclohexyl)disulfide. This invention also relates to the use of 1-n-butoxy-1-ethanol acetate having the structure: ##STR4## in flavors in-combination with 2-phenyl-3-carboethoxyfuran having the structure: ##STR5## and/or bis(cyclohexyl)disulfide having the structure: ##STR6## taken alone or combined further in carbohydrates such as cyclic dextrins to generate acetaldehyde and, at the same time, augment or enhance "grape" flavors.
There has been considerable work performed relating to substances which can be used to impart (or enhance) flavors to (or in) various consumable materials. These substances are used to diminish natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product. Concord grape, wine incense/fruity, pungent, sulfury (berry), minty, musty, weak sweet buttery, sweet carrot, dry woody cinnamon or warm benzaldehye-nut like flavor notes or combinations of these and bitter after taste, benzoate-ester taste and heavy floral backnotes for improving the taste and aroma of artificial grape or other fruity flavoring compositions are particularly desirable for many uses in consumable articles, e.g., foodstuffs.
In U.S. Pat. No. 3,677,772 sulfide derivatives suitable for use in meat flavors are represented by the following structural formula: ##STR7## wherein R represents hydrogen or lower alkyl of 1 to 6 carbon atoms and R.sub.1 represents the carbon atoms necessary to complete a cycloalkyl group, containing from 4 to 9 intracyclic carbon atoms and m is 1 or 2.
Also disclosed in U.S. Pat. No. 3,677,772 is the formulation of cycloalkyl mercaptans in situ with the remaining ingredients of the flavoring or foodstuff composition carried out by employing as the precursor, a mercaptal and/or hemimercaptal capable of yielding the desired cycloalkyl mercaptan by simple hydrolysis, e.g., at refluxing temperatures. Particularly described as suitable for such use is the mercaptal formed on the addition of acetaldehyde to cyclopentyl mercaptan, such mercaptal having the following structural formula: ##STR8## wherein R and R.sub.1 have the aforedescribed significance.
As mentioned on page 442 of "The Chemistry and Physiology of Flavors" (Schultz, Day and Libbey, Avi Publishing Company, 1967), 2-acetylfuran is present in coffee flavors. On pages 218 and 219 of the same publication, ethyl phenyl acetate and 2-phenethyl caproate are mentioned as being one of the volatile esters of wine aroma.
Bis(cyclohexyl)disulfide is prepared according to the process set forth in U.S. Pat. No. 2,517,934 issued Aug. 8, 1950.
2-Phenyl-3-carboethoxyfuran is prepared according to the process set forth by I. H. Kondo and H. Suzuki in J.Pharm.Soc. Japan No. 544,501-5(1927).
In addition, it was indicated in U.S. Pat. No. 3,917,870 issued on Nov. 4, 1975 that solid and liquid foodstuff and flavoring compositions having concord grape, wine, incense/fruity, pungent, sulfuryberry, minty, musty, weak sweet buttery, sweet carrot, dry woody cinnamon or warm benzaldehyde-nut like flavor notes or combinations of these and bitter after taste, benzoate-ester taste and heavy floral backnotes for improving the taste and aroma of artificial grape or other fruit flavoring compositions can be created by the utilization of 2-phenyl-3-carboethoxyfuran and/or bis(cyclohexyl)disulfide in flavor formulae and/or in foodstuffs.
Nothing in the prior art and none of the acetaldehyde precursors either those of German Offenlegungschrift No. 2,802,821 or those of U.S. Pat. No. 3,141,184 teaches that an advantageous flavor and aroma impact be created as a result of using inconjunction with 2-phenyl-3-carboethoxyfuran and/or bis(cyclohexyl)disulfide, 1-n-butoxy-1-ethanol acetate having the structure: ##STR9## whether used alone or whether it is combined with an absorbing solid such as acyclic dextrin.